


Teacher Parent Conference

by Fangirling_FTW



Category: Supernatural
Genre: Alternate Universe, Angst, Angst with a Happy Ending, Doctor Sam, Eventual Smut, F/M, Family Drama, Fluff, Fluff and Angst, It’s me lets be real, John Winchester's A+ Parenting, M/M, Medium Burn, Nurse Castiel, Other Additional Tags to Be Added, Single Parent Castiel, Student Jack, Teacher Dean
Language: English
Status: In-Progress
Published: 2017-12-14
Updated: 2018-04-01
Packaged: 2019-02-14 14:30:39
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 18,597
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13009824
Author URL: https://archiveofourown.org/users/Fangirling_FTW/pseuds/Fangirling_FTW
Summary: Dean just got his first full time teaching gig, and he’s desperate to prove to himself, to the world, and also to his father, that he can do this.  Naturally there’s a student, Jack, that seems to delight in arguing with Dean in particular, enough so that Dean calls in the kid’s parents to have a few words, expecting the same horrible attitude and stubborn arguments from them.Turns out Jack was raised by a single father.  Not only that, a single father who was a nurse at the same hospital his brother works at. This Castiel guy is kinda hot, caring, and totally not what Dean was expecting.  And Dean will come to find there’s a lot more to Cas’ story than meets the eye.





	1. Introduction

**Author's Note:**

> Hey, so MonarchMish on twitter posted this prompt and me and my beta kinda took off with it, and we storyboarded basically the entire story in about three days *fist pump*
> 
> You know me, whatever crap I put these guys through I promise no MCD and happy endings. \o/ I’m excited about this one, it’s an AU Trope I’ve never worked with before, and I’m going to have some fun writing Dilf Cas *smirk*
> 
> Anyway, I will aim for 7-10day updates, but don’t hate me if they take longer! Enjoy!

_Dean_

  
Dean hitched his messenger bag higher on his shoulder as he walked towards the school, trying to keep his head down as he made his way back towards his classroom. Not many students had arrived yet, he was about an hour early than the first bell, but he wanted to get settled before his first class started. He was nervous, though he wouldn’t ever admit it, this was his first real teaching job and he’d sort of packed everything up and moved halfway across the country to take it. His brother Sam had already moved to Florida a couple months ago, so at least he’d had a place to live. Being impulsive wasn’t something Dean did often but apparently when he did act out it was a go big or go home kind of thing.

He walks down the hallways of building 300, the older, musty smell something he was starting to get used to after a week of classroom prep. He gets to his classroom, the third on the left, and unlocks the door, decorated with only a small plaque that said ‘Mr. Winchester’. He smiled and pushed the door open, hitting the lights and making his way back to his desk. He hadn’t done much with the room yet, not exactly sure what to do as far as decoration, and the old cinder block walls made it feel that much more barren. He unpacked the teacher’s copy of the textbook he was using for the term and the stack of syllabi he’d printed and stapled meticulously over the past two days. Sam’s teasing snickers still rang in the back of his head but he ignored it.

  
He was going to be the best damn Algebra 2 teacher this school had ever seen, no matter what anyone said.

  
“Good morning.” Dean nearly trips over his chair as he spins to face his door, smiling when he saw who it was.

  
“Mrs. Mosley,” he sighs, rubbing his hand over his neck in embarrassment.

  
“That’s Miss Mosley,” she huffed. The formidable older woman walked up to him with a knowing smile on her face. She taught the Advanced Placement and Dual Enrollment Calculus 1 and 2 classes, and had been teaching at the school probably the longest out of anyone. Dean deeply admired her the moment he’d met her, and also had learned fairly early on that while she was kind and gentle, she could just as easily crack the whip to keep anyone in line. “I see you went with the tie,” she smirked, and Dean tugged on the green striped fabric self consciously.

  
“Is it too much? It’s too much, isn’t it?” he frets, and he goes to pull it off when her laugh makes him pause.

  
“Honey I think it’s adorable. Really brings out your eyes.”

  
“Thanks,” Dean sighs, turning from her as his eyes roam the classroom.

  
“Just remember, while you may be the teacher, it doesn’t mean these kids can’t teach you a thing or two,” Miss Mosley hums. The sounds of kids filing into the building set his blood pressure rising and he takes a couple deep breaths.

  
“Here we go,” he sighs.

  
His first period class was fairly subdued, but Dean reasoned it was probably due to lack of sleep and the fact that all he was doing was handing out their syllabi and reviewing a little of algebra one to get an idea of where each class was. He had four classes before lunch, and then one after, and it had all been smooth sailing enough that he was starting to feel confident in this whole teaching thing.

  
Then his sixth period class came in.

  
He’d been warned by his professors and by other teachers that everyone had that _one_ class, the one that happened to have all the troublesome students in it, and that gave the teacher the most grief. Half the class came in just as the last bell was ringing, and a handful stumbled in a few minutes after that. As he took roll the students grudgingly answered, and Dean tried not to let it get to him. This was their sixth class of the day, the sixth time they’d taken roll, the sixth syllabus they’d been handed, he knew they were getting tired.

  
Dean starts to review what they should have learned last year, at least by his lesson plans, but by the blank, or openly annoyed, looks from the class he might have a bit more work to do with this class.

  
“Okay,” Dean sighs, writing an equation out on the board and turning back to the class. “Who can tell me what to do first?” The silence he was greeted with was borderline creepy, and he scans the classroom until someone makes eye contact with him. A tousle haired boy who had taken the seat farthest from his desk, and was currently watching him with a disinterested look on his face. “Um… Jack, right?” he calls on him, and the boy pushes his dark blonde hair out of his face.

  
“What?” the kid sighs.

  
“Can you tell me what to do first in this problem?” Dean asks calmly.

  
“No.” The blunt answer startles Dean a bit.

  
“Why not?” Dean presses

  
“You’re the teacher, you’re supposed to teach me,” Jack shrugs, sounding almost bored, and a few of the other students snicker.

  
“This is something you should already know,” Dean says calmly.

  
“In that case why are you reviewing, if we already know it?” Jack reasons to more snickering.

  
“Because the whole point of this is to figure out what you remember,” Dean says, breathing deep to maintain his patience.

  
“Ugh,” someone groans from the other side of the classroom. Dean turns to see a girl with a huge mess of blonde hair pushing herself to her feet, moving up to the board and grabbing the marker, solving the first step of the equation, and storming back to her seat.

  
“Thank you, uh…”

  
“Claire,” she huffs, scowling at Jack. “Sorry, but some of us want to spend as little time trapped in this stupid place as possible.” Jack sneers back at her, and Dean shifts uncomfortably at the board.

  
“Um, okay, how about someone else for the next step?”

  
To his relief a couple hands went up, and the rest of the review went a bit more smoothly. It seemed that the class as a whole understood the subject matter, but the attitude problem was something Dean knew would make his job difficult. When the bell rang, Dean moved towards Jack’s side of the room. Maybe sensing he was trying to be stopped, Jack ducked his head and started to hurry for the door, but Dean beat him to it.

  
“Mr. Milton,” Dean began.

  
“Don’t call me that,” Jack snapped. “My dad is ‘Mr. Milton.’”

  
“Okay, Jack,” Dean tried again. “I’m not sure how we got off on the wrong foot-”

  
“Just stop,” Jack sighs. “Don’t give me some speech about trying to be my friend, I don’t want it, I don’t need it.” The anger this kid was projecting was almost strong enough to make Dean take a step back.

  
“Okay, I can respect that,” Dean nods. “Just know I’m on your side, okay?”

  
“Whatever,” Jack sighs, pushing past Dean and out the door. Dean catches a whiff of sandalwood off the kid’s clothes and he’s pulled into a memory against his will.

 

“ _You don’t know a thing about me, or my dad, so just stay out of this!” The smell of the wood shavings under his feet is thick in his nose._

_  
“I know you’re more scared of him than you’ll admit, boy. You don’t hide it as well as you think.” Dean glares at the man chastising him like a little kid, tugging on his Dad’s leather jacket to pull it tighter across his shoulders._

_  
“I ain’t scared,” he huffs defiantly._

_  
“Then why haven’t you left, like you were always saying you would?”_

 

Dean physically shakes himself out of his own memory, unnerved by how much Jack reminds him of himself.

  
His seventh class period was his planning, and since he didn’t have anything to grade he simply filed his attendance reports and packed up, locking his room and closing the door behind him. Campus was quiet since the kids were still in class, which meant he could slip out fairly unnoticed. Pushing open the door to his building he turns onto the main walkway and He was just tugging off his tie when he’s nearly knocked to the ground as someone collided with him, followed by a startled oof. Dean spins to see a red head pushing herself to her feet, her outfit just as scatterbrained as her belongings she was quickly attempting to scoop up. It took Dean noticing her teacher’s badge to realize she wasn’t a student.

  
“I am so sorry, I just wasn’t paying attention and, holy crap you are built like a truck I just bounced right off of you and hit the pavement and-“

  
“It’s okay,” Dean interrupts, cutting her off so she could breathe. “I’m Dean,” he offers his hand, and she shuffles her things into one arm to shake it.

  
“Oh, you’re the new guy in the math department! I’m Charlie Bradbury, I teach computer science!” The way she said ‘you’re’ like people had been talking about him made him a little nervous, but he smiled at her anyway.

  
“Nice to meet you, Charlie.”

  
“So they gave you seventh period planning?” she asks as they continue walking through the hallway.

  
“Yeah, figured I could sneak out early today.”

  
“Same,” she sighs. “Not a whole lot to do the first day. Did you choose to teach math or was it kind of thrust upon you?”

  
“I’ve always been good with numbers,” Dean explains. “I figured math would be easy to teach for me.”

  
“I kind of envy you,” Charlie admitted with a sigh. “Teaching computer anything to kids in this generation is so difficult because they think they know everything.”

  
“It doesn’t help that teens in general think they know everything anyway,” Dean shrugs as he stops at his car.

  
“Let me guess, you already have a trouble student?” she asked.

  
“I guess,” Dean shrugged. “I mean, I know not to take it personally, it’s obvious this kid has something else going on, but…” he trails off and shrugs.

  
“Just prove to them you know more about something they like and watch them tremble before you,” Charlie laughs.

  
“What?”

  
“You know, something that earns their respect. For me I can out game any of them, and even the ‘cool’ kids have something they’re obsessed with. Prove to this kid you know more than him about whatever that is and watch his attitude change.”

  
“That’s… not the kind of advice I was expecting,” Dean chuckles.

  
“Whatever works,” Charlie laughs. Dean stops walking at his car, and Charlie pauses with him. “Hey, if you ever need help with anything, I’m in building 800, room 804 is the computer lab. We share a planning so if you need time to clear your head, feel free to drop by.”

  
“Thanks,” Dean said sincerely, smiling at her as she turned and continued walking through the parking lot.

  
The drive home wasn’t pleasant, especially since his 1967 Chevy wasn’t exactly designed for low mpg city traffic, but he refused to either take the bus or get a new car, so he’d just have to suck it up and pay for all the extra gas. Sam had an even worse commute, heading into the heart of downtown Orlando every day, so Dean really didn’t have room to complain. They lived in a fairly decent apartment complex on what Sam referred to as the ‘good side’ of Metro West and what Dean referred to as ‘overpriced’, but with some savings Dean brought with him and Sam’s job at the hospital they made it work. Dean pulls into the parking lot and parks in front of their building, making his way upstairs and unlocking the door.

  
“Hey,” Sam calls from the couch. Dean waves and drops his keys in the bowl next to the door, kicking off his shoes and yanking his tie off. Sam had just finished a 24 hour round in the ER, but after two days off he was finally starting to look more himself again.

  
“Seriously,” Dean sighs, “I mean, I should commend you because I’m a teacher but you’ve already graduated.” Sam looks at the books he’s half buried under on the couch and shrugs.

  
“I can’t learn too much in this profession, Dean.”

  
“Okay, Dr. Strange,” Dean huffs, tugging his button up off and leaving himself in his undershirt and khakis.

  
“How was your first day?” Sam calls, ignoring Dean’s poor attempt at an insult.

  
“Not bad,” Dean shrugs. “Not as scary as I thought it would be.” He pokes around the kitchen for a few minutes before finding enough to cobble together a dinner of sorts. It was just some frozen vegetables and spaghetti noodles, but tossed in some soy and teriyaki sauce he could make it edible.

  
“Any kids give you any grief?” Sam asked.

  
“Just one,” Dean admitted, putting a pot of water on the stove to boil. “Reminds me a lot of me, which is scary enough as it is.”

  
“High school you?” Sam asks, looking up in renewed interest.

  
“Yeah,” Dean sighs, watching the pot as he waits for the water to heat. “I mean, I was pretty fucked up back then, Sammy, but that kid looked at me and…”

  
“Hey,” Dean looked up to see his brother had joined him in the kitchen. “You’re not that guy anymore, Dean.”

  
“I know that,” he grouses, shrugging off Sam’s concern and gathering some spices off the spice rack. He focus on starting the pasta, ignoring his brother’s concern and definitely ignoring his stroll down memory lane.

  
He had moved on, and there was no looking back.

 

 

*****

 

 

_Castiel_

 

Castiel’s feet were killing him, but he had survived the 14 hour shift in the ICU. He made his way towards the locker rooms, glancing at the clock as he walked down the hallway. There was just enough time for him to get home before Jack, if traffic was forgiving. Stepping into the men’s room, he strips out of his scrub bottoms, grabbing his regular pants out of his locker.

  
“Well, hello.” Cas nearly fell over, catching himself on the lockers and finishing pulling up his jeans.

  
“Meg, this is the men’s room,” he sighs.

  
“So?” she asks, walking up and sitting on the bench next to him. Meg was abrasive, rude, anti-establishment, and somehow had wound up being Castiel’s best friend since he’d switched majors from Biology to Nursing almost 18 years ago.

  
“So other people might object to you violating their space.”

  
“They can deal. So, it’s the spawn’s first day of school today!” Her voice titters gleefully as Cas shuts his locker.

  
“Don’t call him that,” he replies out of habit. She never listens, and strangely it’s actually turned into an affectionate term between her and Jack.

  
“Whatever. You figured out what’s going on with him?” she asks, following along behind him as he leaves the locker room and heads towards the parking lot.

  
“No,” Cas admits. “I mean, I get that it’s the whole teenager MO to be distant and surly, but he won’t talk to me.” Cas wasn’t sure why, but about a week ago Jack had suddenly closed off, taking to shutting himself in his room where he usually spent the night on the couch, and he’d stopped talking to Cas almost completely. He wouldn’t have been as worried if it had been more gradual, but this had happened almost overnight, one day he’d just woken up with a whole new attitude. At first, Cas had let it be, but when he’d given in and pressed Jack for information, Jack had completely shut him out, literally locking Cas out of his room.

  
“Do you want me to feel things out?” Meg asks. “See if he’ll talk to me about it?”

  
“No,” Cas says quickly. “He’s never kept anything from me before, I’m sure he’ll come around.”

  
“You trying to convince me or yourself?” she asked knowingly. Cas didn’t bother to answer, he just climbed into his Corolla and started the engine. She rolled her eyes and waved through the window as he pulled away, turning for home.

  
It had been 16 years since he’d suddenly, and quite surprisingly, been faced with the prospect of raising Jack alone. Jack’s mother, Kelly, had died in childbirth, and Cas had been doing the best he could as a single parent with few friends and no family of his own to help. He’d tried to make sure Jack never noticed the strain it had placed on Castiel, working double shifts with only small gaps in between to be home for Jack before whisking him away to daycare or school and doing it all over again. Jack did well in school, and was usually a very warm, happy kid, so Cas figured he’d generally done something right.

  
Downtown traffic was horrible as usual, but he made fairly good time, driving down some side street short cuts he’d discovered over the years. As he approached the edge of the main downtown area and neighborhoods started to open up, traffic thinned out and he made it home without too much hassle. They were renting a small two bedroom apartment for fairly cheap, all things considered. Even with their proximity to downtown, and the decent neighborhood, the apartments themselves had fairly small living rooms and kitchens, and since Cas didn’t really have that many people to invite over, he and Jack made due.

  
After finding a parking spot and making his way upstairs to the second floor, Cas bumped into his favorite neighbor, Eileen Leahy. She had moved in almost two years ago, and since she was deaf, Cas was thrilled he had someone to practice signing with. Cas had learned ASL while in college, after deciding to become a nurse he figured it might come in handy. She had taught herself how to speak fairly well, and Cas helped her practice with that, the two of them bonding quickly. Cas caught her attention and she beamed at him.

  
 _Hello_ , she signed quickly, _school started today right?_

  
_It did. I think I made it home just before Jack._

  
_Your tall friend isn’t visiting today?_ She asked with a giggle. One of the new doctors, a Dr. Sam Winchester, had been over to visit a few times since he’d started at the hospital, being all alone in a strange city. Cas knew the feeling and wanted to welcome the young man to the town and the hospital, and they’d become fairly friendly. And both he and Eileen had taken a liking to the other ever since he’d tried to sign thank you to her and told her something… not quite as friendly.

  
 _Not today. You know, I could just give you his phone number, you could text him._ She blushed and shook her head, and Cas laughed, waving goodbye as he unlocked his apartment door and she turned for the stairs.

  
Tossing his keys on the table, Cas made his way to his bedroom, changing into a tshirt and walking back out into the kitchen to get the oven started for the frozen lasagna they were having for dinner. It’s not that Cas couldn’t cook, it’s just that more often than not he didn’t have enough time to do it, so he’d fallen out of practice and into the habit of making something that could be zapped in a microwave or baked in an oven.  
With dinner started Cas starts contemplating how long he’d stay awake if he sat on the couch, but he’s saved from having to find out when the front door opens, Jack walking in and tossing his keys on the table next to Cas’. He doesn’t look at Cas, kicking off his shoes and dropping his backpack on the couch.

  
“Hey, how was your first day?” Cas optimistically attempts a conversation.

  
“Fine,” Jack shrugs. “New math teacher.”

  
“Is there anything I need to fill out? Did you have all the schools supplies you’ll need?”

  
“Yeah,” Jack says flatly, shrugging out of his sweater and turning for his room.

  
“I’ve got dinner in the oven, can you listen for the timer in case I fall asleep?”

  
“Okay.” And with those last two syllables, Jack shuts the door to his room, cutting Cas off from asking him anything else.  
Well, it went better than Cas thought it would, anyway.

  
At the risk of passing out, Cas drops onto the couch and stares across the room at the DVD cabinet, eyeing the photos sitting on the shelves. Pictures of him and Jack, with a few of the two of them and Meg dotted in between. There’s a couple old photos of Cas and his sister, Anna, but he hadn’t spoken to her almost since Jack was born, and he drops his gaze from them quickly.

 

_“Help me understand why this is your responsibility.” Anna’s arms are crossed, and Castiel doesn’t flinch away from the look of disgust she’s not even bothering to hide._

_  
“It’s human decency, it’s what she wanted-”_

_  
“What about you, Castiel? How do you expect to live your life?” she scoffs. “You can’t really expect me to believe you want this...thing.”_

_  
“Fuck you!” Castiel snaps, and Jack’s cries from the other room seem to be the final straw for his sister._

_  
“Fine. I hope the two of you have a wonderful life.” She spins and walks out the door, and Cas makes up a bottle as quick as he can, trying not to cry his own tears as he tends to the infant._

Cas sighs heavily, getting up to find something to keep him awake besides worry.


	2. Chapter 1

**Summary for the Chapter:**

> Finally detention ends, and the kids scurry out of the room. Jack seems to be expecting Dean to stop him on his way out, but when Dean lets him go, he makes the mistake of letting a brief moment of triumph show on his face. Once the kids are gone, Dean shifts his attention to his computer, pulling up the email address listed for Jack’s parents. The only one listed is for his father, so Dean selects it and starts to type up an email requesting a teacher parent conference. He’d done taking this kid on alone, he needs to know what the hell is happening in his home life to make him so aggravating.

**Notes for the Chapter:**

> Okay, full chapter, here we go! Just some more character introduction and establishment, the next chapter things are going to start moving XD

_Dean_

Dean massages his temples, willing away the headache lurking behind them as he bent over his meager lunch at his desk.  He tugs at his sweater, getting it low enough to undo the top couple buttons on his white dress shirt underneath, glad he’d decided to skip wearing the tie today.  He’d take the sweater off if it wasn’t so freaking cold in his classroom, no matter what the temperature outside it was always freezing in here.  He could have worn a school polo, since Friday was supposed to be spirit day, but he just wasn’t looking forward to Friday’s anymore.  Apparently the teacher who usually handled Friday detention had quit last year to pursue their Master’s degree, and Vice Principal Adler had decided to saddle Dean with the responsibility of taking their place.  Not wanting to argue and get assigned to do Saturday, too, Dean just accepted it with a fake smile.

Now, six weeks of Friday detention later, Dean was starting to feel regret for every life choice he’d ever made.  In need of caffeine, he finishes his sandwich and leaves his classroom to head for the teacher’s lounge and the coffee pot they kept full 24 hours a day.  As he passed by the soda vending machines near the student lunch room he noticed two students not so subtly making out in the corner.  With a heavy sigh, Dean walks up behind them, clearing his throat loudly.

“Alright, fellas, no making out in the hallways.”  One of the boys jumps back, his face flushing as his eyes fall to his feet.  

“S-sorry, Mr. Winchester.”  Clarke, Dean recognizes him from his fifth period class.  The boy he was kissing huffs a weary sigh.

“Technically, we weren’t in a hallway.”  Jack Milton is leaning on the wall, eyebrow raised in annoyance, and Dean barely refrains from facepalming.  He and Jack hadn’t exactly mended their relationship since their first interaction, if anything he’d become the one student Dean did _not_ look forward to seeing.

“Okay, Clarke, since this is the first time I’m catching you, you get a warning,” Dean says in his best stern teacher voice.  Clarke nods, shooting a glance at Jack before hurrying away down the hallway.  Dean turns his attention to Jack, who tosses his wavy hair back from his forehead with a twitch of his neck.  “What happened to the girl I caught you with last week?” Dean asked sarcastically.

“Got bored.”  Jack has become scarily good at pushing Dean’s buttons, and Dean can only imagine what assholes he lives with to make him like this.

“Well, hopefully you’ll have plenty of homework to work on in detention,” Dean sighs.  

“Oh, I already have Friday detention this week, _sir_ ,” Jack says smugly.  Dean pulls the slips out of his pocket anyway and fills one out for Saturday, handing it to him with his own smug smile.

“See you in class today,” Dean calls, turning and walking back towards the teacher’s lounge.

“Seriously?  For kissing a boy?!  Homophobe,” Jack grumbles.  

“Okay one,” Dean huffs, stopping and walking back up to Jack angrily, “I’m not homophobic, and two, it’s the third time I caught you, with three different kids I might add.  No more warnings, you know the rules.”  

“I can’t get to school on Saturdays,” Jack whined.

“Take the city bus, just make sure you leave early,” Dean called over his shoulder, _really_ ready for that caffeine now.  He makes his way into the teacher’s lounge, pushing the door open and glancing around to see who was there.  With midterms coming up soon a lot of teachers were spending their lunch breaks in their classrooms to write up tests, so most of the faculty in the lounge were from athletics or the arts.  He waves at one of the football coaches, Benny Lafitte, before moving to the coffee pot and pouring out a cup of coffee, dumping two packs of sugar into it.  Charlie is sitting at Benny’s table, and waves cheerily as Dean approaches with his liquid reinforcement.

“This doesn’t bode well,” Benny chuckles as Dean walks over to sit next to him.

“Just a headache,” Dean sighs.

“What’s it’s name?” Benny jokes.  Dean grimaces and takes a sip of coffee.

“Jack Milton.  We’ve been a bit at odds since school started, I’m not sure why.”

“It’s not just you,” a voice chimed in from behind them.  Dean turns to see Billie St Clare, or Miss Billie; even the kids called her by her first name.  She taught the upper level art classes at the school, and was generally respected by everyone on campus, teachers included.  “He’s a quiet kid, but he’s also kind and very giving.  Since this school year started something’s been off about him, though I have no idea what.”

“So it’s not just me?” Dean asks.

“No, I don’t think so.  Though for all I know he could have a personal beef with you,” she adds with a smirk.

“Gee, thanks,” Dean sighs, chugging his coffee as Benny chuckles.

“So is today the day?” Charlie’s voice chimes in, changing the topic deftly.

“Doubt it,” Dean sighs.  She’s been trying to get him to one of the school’s home football games, and even a couple of the away games, every week since they started, and Dean’s answer is always the same.

“Aww, come _on._  What is there to be afraid of?”

“Pubescent teenagers and bad high school flashbacks,” Dean counters.  Charlie considers that a moment before nodding.

“Fair enough,” she concedes.  “But you could also have fun.  You know, that thing that happens when you go out with your friends for drinks afterwards?”

“Pass, Charlie.  I’m not the social type.”

“Miss Braeden wants to change that,” Benny adds, grinning smugly as Dean shoots a glare at him.  

“I’m sure Lisa is lovely,” Dean shrugs, standing and moving back to the coffee pot for a refill, “but I’m just not looking for that right now.”  Miss Billie gets up from her table with an amused hum, and Dean flushes with even more embarrassment.

“Okay fine,” Charlie sighed.  “At least come over to my place for nerdy movies and lunch on Sunday?”  She was unashamedly giving him the puppy dog pout now and Dean smiled.

“Okay, Sunday,” he promised.  She grinned, walking out of the room with a bounce in her step as Dean dropped back into his seat across from Benny.

“Seriously though, why so reluctant?” Benny asks.  Dean shrugs, swallowing more coffee in lieu of answering and Benny lets it go.

Turns out three cups of coffee didn’t help too much with his headache.  

Before Dean knows it his planning period is over and the Friday detention group is filing into his classroom.  Three of them are the usual suspects Dean has come to know, both from his classes and the fact that even though it’s only eight weeks into the school year some of them have been here before.  Jack sulks into the room, glowering at Dean once before dropping into his desk, and he’s followed by Claire who drops into her own seat and kicks her legs up on the desk.  The two of them have a rivalry of sorts going on, since both of them were very smart but had attitudes the size of Montana.  Kaia Nieves, a girl Dean’s hardly heard speak five words, tucks herself into a desk, her hoodie pulled up over her head and her arms crossed.  Another four Dean hasn’t personally met before round out the group, and Dean shuts the door once he’s collected their detention slips.

“Okay guys, no talking, just catch up on some homework,” Dean sighs, pulling a stack of papers that need grading towards himself.  Glancing around the room to make sure all the kids are getting out something to do, Dean turns his attention to his own work.  A few minutes go by in relative quiet before a soft tapping noise starts from the back of the room.  Dean tries to ignore it, knowing _exactly_ which kid it is without even looking, but when a couple of the other kids start to shift in their seats, Dean clears his throat and looks up at Jack.  Jack feigns a look of innocence and stops tapping his fingers on his desk, and silence falls over the classroom again.  This time it lasts for all of ten minutes until the clicking starts up again, this time from a pen.  Dean manages to make it a few minutes longer, but when the other kids start to click along with the beat, adding their own flourishes he clears his throat and turns a scathing look up at the room in general.  Most of the other kids bow their heads but Jack smiles in triumph, and Dean takes a deep breath, waiting for Jack to continue reading before he goes back to grading.

Fifteen whole minutes go by, and when Jack starts up again, this time he’s tapping out a rhythm with his feet.  They’re only halfway through detention, and Dean starts to bemoan his very existence.  Raising his eyes in a brief _why me_ he drops them again and doesn’t even bother glaring at Jack, just stares blankly until the kid grows tired of his game and stops.  Claire clears her throat, and Dean watches in amusement as she and Jack have a silent conversation.  Eventually, it seems she wins and Jack sulks in his chair, hiding behind Canterbury Tales, and Claire smiles sweetly at Dean.  It’s not a comforting smile.

 _Finally_ detention ends, and the kids scurry out of the room.  Jack seems to be expecting Dean to stop him on his way out, but when Dean lets him go, he makes the mistake of letting a brief moment of triumph show on his face.  Once the kids are gone, Dean shifts his attention to his computer, pulling up the email address listed for Jack’s parents.  The only one listed is for his father, so Dean selects it and starts to type up an email requesting a teacher parent conference.  He’d done taking this kid on alone, he needs to know what the hell is happening in his home life to make him so aggravating.  He starts and stops a few times, and when it’s finished he reads it a couple times, hoping it sounds professional enough.  

_Mr. Milton,_

_My name is Mr. Winchester, I’m Jack’s Algebra 2 teacher.  While Jack’s grades have been acceptable, his attitude has left a lot to be desired, specifically when it comes to myself.  I was hoping we could meet at your earliest convenience to discuss Jack’s behavior.  I want him to succeed, he’s a smart young man and he deserves to have the best chance he can get.  Please feel free to email me back at this address._

_Thank you,_

_Mr. Winchester_

As Dean walks to his car a few minutes later, he notices Claire and Jack waiting at the pick up area for their ride home, chatting and acting completely different than they acted in class.  Dean could see they were close friends, they’d probably been in a lot of the same classes through the years, and he wasn’t exactly sure why there was such fierce competition between them in the actual classroom.  A kind looking woman with dark cropped hair pulls up in a pickup truck, and both kids climb inside, leaving Dean to ponder the complexities of this Jack kid yet again.

 

After an agonisingly long drive home, Dean closes his apartment door behind him, dropping his keys in the bowl.  Sam had sent him a text as he was driving home about running late, so the apartment was empty and quiet.  Dean’s tempted to just go to sleep, but it’s way too early, he’d just end up awake at 3am.  He searches the kitchen for something to eat, tossing some leftover chicken and mashed potatoes in the microwave.  

He never really had that many friends to begin with, ever since he was young he’s always been sort of a loner.  His mother’s death when he was 4 probably had something to do with that, but Dean’s always been happy with just a couple close friends, and every now and then a boyfriend or a girlfriend.  The moment he got his degree, he’d uprooted from Kansas, packing up his life and moving to Florida without looking back, and even with his lone wolf tendencies, the loneliness was starting to creep up on him.  He glances at his overstuffed messenger bag full of papers, and shakes himself out of his funk.  He had work to do, he didn’t have time to mope about this.  

Dean spread his things out across the dining room table, getting about a quarter of the way through his grading before Sam finally walks in from work.

“Hey,” he sighs, dropping his duffle on the floor by the couch and setting a bag of takeout from Chipotle on the table.

“Dude, you look awful,” Dean points out.  Sam always looked exhausted lately, between working his shifts at the hospital and studying for his specializations, he knew his little brother must hardly get any sleep.

“Thanks a lot,” Sam chuckles.  “Anyway, I’ve managed to get the weekend off, we can watch the game tomorrow,” he adds, going into the fridge and getting them each a beer.

“That’s good, Sam, you could use an extra day off.”  Dean takes the beer, eyeing it suspiciously.  “I probably shouldn’t drink while I’m grading,” Dean points out.

“Afraid you’ll just give them all A’s?” Sam laughed.

“No, afraid I might fail them all,” Dean answers honestly.  Sam laughs and scoots Dean’s stack of papers aside so he has some room, the two of them lapsing into silence while he eats.  Dean can tell Sam wants to ask him something, and by the time his little brother has finished his burrito bowl he finally seems to have worked up the courage.

“Listen, I uh, I know we don’t spend much time together, but I was going to go visit a friend on Sunday,” Sam stammers.  

“I’ve been invited to Charlie’s on Sunday, so that works,” Dean shrugs.  Pausing, he eyes Sam carefully.  “By the way, am I ever going to meet this friend?” Dean smirks.  “Or the girl you’re using him as an excuse to go visit?”  

“I- I, uh,” Sam clears his throat, his ears turning red.  “Shut up,” he grouses, pushing himself to his feet and gathering his trash.

“Dude, I’m just saying,” Dean chuckles.  “Unless… is it the ‘friend’ that is making you all twitterpated?”  Dean gets a bottle cap thrown at him for his teasing.  “Hey, I don’t judge!”

“Yes, okay, fine, there is a girl,” Sam admits grudgingly.  “She’s got a beautiful smile, and she’s so smart and funny…”

“And?”

“She’s deaf,” Sam admits.  

“I’m pretty sure your heart eyes translate into non-verbal communication,” Dean laughs.  Sam pulls a bitchface and Dean shuts up.

“I’m serious about this, Dean.  I’ve been studying up on ASL, even.  I just...I want to try and do this right, not as a one nighter or a pickup, you know?”  Sam’s earnest determination sobers Dean’s teasing.

“Okay, Sammy, I get it,” he nods.  “I still want to meet her.”

“And I will introduce her,” Sam insists, “once I’ve figured out what the hell I’m doing.”  Sam sips at his second beer as Dean goes back to grading.  There’s something else on his brother’s mind today, apparently, and Dean sets his red pen down with a heavy sigh.

“What else, Sam?”

“I uh, spoke with Jo this morning.”

“I don’t want to know, Sam.”  Dean’s mood sours immediately, the food he’d just eaten churning nervously in his gut.  The thing was, he really does want to know, but he can’t exactly admit that, not when he’s been putting up this facade for Sam’s benefit ever since moving in with him.

“Look, I get it, okay?  Dad’s a dick, but he’s _dad._ ”

“No,” Dean grunts, marking so hard on some poor kid’s worksheet he rips a hole in it.  “He told me if I left then it was for good.”

“I’m not saying he doesn’t deserve this,” Sam sighs, “I’m just saying there are other people you’re shutting out.”  

“You think I don’t know that?” Dean scoffs, gathering up his things angrily.  

“Dean-”

“Whatever, Sam, I’m going to bed.”

“Come on, don’t be like this-”

“Like what?” Dean snaps.  “Pissed off?  Like _Dad_ maybe?”  Whatever Sam was going to say stays stuck behind the lips his brother has pressed together.  Dean stalks off to his room, dropping the stack of papers to be graded on his desk and then dropping himself into bed, clothes and all.

Well, wasn’t that the icing on top of a shitty day?

He doesn’t need to hear from his brother, who heard it from his best friend Jo, who heard it from her mother, how his father was coping now that his prodigal son had abandoned him.  Dean felt enough guilt on his own, he didn’t need a stupid childish game of telephone to add to it.  He rolls onto his stomach, hugging his pillow and trying to remember he was 30 years old, turning 31 in a few months, and he was _teaching_ mopey teenagers, so acting like one wasn’t exactly the best plan to deal with this.

He reaches back and tugs his phone out of his pocket, checking to see if he had any new email in his teacher’s account before heading to bed.  Opening it, he was surprised to see a response from Jack’s father.

_I have space in my schedule for Monday afternoon._

_Mr. Milton_

That was it.  One sentence.  He’d half expected some righteous indignation about how his son was perfect and this meeting couldn’t possibly be necessary, or maybe an apology if Jack was equally a nightmare at home.  One sentence almost made it seem as if this Mr. Milton didn’t even care enough about Jack’s issues at school to be annoyed.  Dean’s stomach turns at the thought of how _his_ father would have reacted, and he doesn’t know which one is worse.  He grudgingly climbs out of bed to undress and brush his teeth, crawling back under the covers and drifting into an uneasy sleep.

 

_“No, I’m done letting you make decisions for me.  I’m my own person, with a mind of my own, and I’m going to do this!”_

_“The hell you are, boy!” John’s voice thundered, coldly threatening in both it’s volume and tone._

_“Sammy, just get out of here!” Dean shouted as he jumped between John and his little brother, tears he doesn’t dare shed clouding his vision.  Sam grabbed his bag and darted for the door, and a few moments later Dean heard the rattle of him biking away as fast as possible.  John screamed a series of expletives, and Dean heard something shatter against the wall, but he doesn’t turn, just stays completely still and hangs his head, waiting for the storm to pass._

_“Fucking ungrateful piece of shit!”  John’s anger is thick enough to suck the air out of the room, but still Dean doesn’t move.  “I’ve done all I could for you boys, and he goes and abandons us, his family, over some fucking girl?  Fucker better not call me and ask for a single dime!”  John shattered something else, and his footsteps stormed off upstairs, rattling the entire house as he heads for his room and the stash of liquor Dean knew he has up there._

_Silently, Dean cleaned up the mess, like he’d done for the past 18 years, ever since he was four years old.  Silently he resigned himself to just listening to his dad’s barked orders, his dad’s plan for him, and silently he wished he had the balls to do what Sammy did.  He doesn’t cry till he’s locked in his room, face buried in his pillow to hide any audible sobs.  It’s the only place he lets himself cry, the only place he feels safe enough from his father’s wrath to let himself feel how shitty his life is._

 

Dean wakes up around 1am, wipes the tears from his face and turns his pillow over to the dry side before dozing off again.  

  


*****

_Castiel_

“Are you serious?” Meg asks, leaning over Cas’ shoulder to read the email.  Cas can’t believe it, after 11 years of near perfect behavior he’s being called in for a teacher conference over Jack.  Cas was so shocked by the contents of the email he hadn’t bothered to keep Meg from reading it, and now the other nurses in the breakroom are glancing at them out of the corner of their eyes curiously.

“Has he really gotten that bad?” Cas wonders aloud, sliding his phone onto the table.

“Hell no!” Meg scoffs.  “This is that new teacher, right?  He’s probably got something to prove, so he’s got a stick up his ass and wants to make an example out of Jack.”  She leans back in her chair next to Cas, nudging him with her elbow.  “Hey, sourpuss, it’s not the end of the world.”

“What did I do wrong?” Cas wonders.  “What have I missed that’s bothered him this much?”

“Dude, seriously?”  Cas can hear Meg rolling her eyes.  “Cas, you didn’t do anything wrong.  He’s 16 years old, I’d be more worried if he wasn’t acting out.”

“Maybe I should talk to Jody,” Cas reasons.  Jody Mills was a local cop who fostered teens in trouble, and her house in turn became one of the after school hangouts.  Cas wasn’t worried about letting Jack visit, Jody had the help of another officer Donna Hanscomb, and with state laws to keep in mind the kids were never unsupervised.  Currently she had two wards actively living at her house, one of whom he knew Jack was good friends with.

“I mean you could, or you know, you could just talk to Jack,” Meg points out.

“I’ve tried,” Cas sighs.  “But how else do I ask if anything is wrong without saying ‘I don’t believe you,’ or ‘I think you’re lying?’”  

“Dunno Cas,” Meg shrugs.  “You’re the parent, not me.”  Cas opens his mouth to argue, but the call goes out over the intercom for them to return to their stations.  “Back to it,” Meg sighs, and Cas grabs his phone, pushing to his feet and typing a quick response to the email as he hurries through the corridors.

Cas stumbles through the locker room door a couple hours later to find Sam Winchester in the process of changing out of his scrubs.  He had the look in his eyes, the one Cas has come to know so well after working in a hospital for 18 years.

He lost someone today.

“Hey,” he says gently, moving towards Sam slowly with his palms outstretched.  “You gonna be okay?”

“Yeah.”  Sam forces out a sigh, shaking his shoulders slightly as he tugs his jeans up.  “Yeah, Cas, I’ll be okay.”  Cas takes off his own scrubs, pulling his clothes out of his locker.  “There was nothing we could do, you know?” Sam continues.  “But at least they weren’t hurting.”

“Why don’t you come over on Sunday,” Cas asks as he buckles his jeans.  “I’ll have Eileen over, and maybe Meg, we can have a big lunch.”  Cas shrugs into his shirt, turning to look at Sam.  “If you need to talk, great.  If not, great.”  Sam smiles, his posture relaxing as he toys with the shirt in his hands.  Cas kinda wishes he would put it on because the size of Sam’s shoulders and pecs sort of makes him feel inferior.

“You’re good at that, you know.  Makes sense why they call you the whisperer.”  Sam tugs on his shirt and Cas blushes at the nickname.

“Here I am, trying to be nice, and I’m getting picked on for it.”

“Sorry,” Sam chuckles.  He gathers his things, patting Cas on the shoulder as he walks out.  “See you Sunday, Cas.”  Cas gathers his own things, turning to walk out of the locker room after Sam.

The nickname of ‘whisperer’ was something he’d earned shorty after arriving to work at the hospital.  Jack was a newborn, and Cas would slip into the on-site day care to check in on him fairly regularly.  The women in charge of the kids would joke that as soon as Cas walked in the room, the babies would all stop fussing.  People started to call him in for help with stubborn or belligerent patients too, and Cas would be able to calm them easily enough, getting them to take medication or allow a doctor to help.  

Cas refuses to believe he has some magical aura that makes his presence soothing to people.  He’s just good at his job.  It helps that he’s learned as many languages as he can, so that’s not usually a barrier for him, and with all that he’s been through in his life he doesn’t panic as much as some people do.  Still, the nickname stuck over the years, and now he finds himself being paged to all corners of the hospital when people need help with difficult patients.  He was debating going to the administration and demanding a job title be made for him so he could get paid more.

When he gets home to an empty apartment, he remembers the email he’d received from Jack’s teacher and puts that level headedness to use, trying not to blame Jack or the teacher before talking to his son.

Doesn’t stop him from blaming himself.

Cas waits in the living room until Jack comes home, walking through the door with his head down like he knows he’s in trouble for something.

“Hey, Jack, can I talk to you for a second?” Cas calls, and Jack stops and turns back for the living room, dropping down in the chair across from Cas.  

“Sorry I’m late getting home, Jody had to take a business call and couldn’t leave the house till she got it,” Jack explains.

“That’s fine, she texted me when she picked you up.”  Cas pulls his phone out of his pocket, watching Jack for his reaction.  “I got an interesting email today.”  Jack’s eyes go wide and he pales slightly, looking up at Cas in surprise.

“I...look, I didn’t…”

“Why is your teacher, this Mr. Winchester wanting to talk to me?”

“Wait, what?”  Jack’s surprise fades into confusion.  “ _He_ emailed you?  What did he say?”  Cas is confused by Jack’s reaction, but he continues anyway.

“He wants to meet with me, about your apparent ‘attitude problem’ according to his email.”

“He’s just picking on me,” Jack shrugs.  “He’s new, he doesn’t get me.”

“Jack, _I_ don’t get you lately, and I’m your father.”  Cas sighs heavily, running a hand over his face.  “You don’t have anything to prove, you know.  If the reason you’ve been so out of sorts lately is another kid at school-“

“Just stop,” Jack grunts, pushing himself to his feet.  “Nothing like that is happening.”

“There’s _something_ you’re not telling me, and I don’t think I’m going to let you go to Jody’s anymore until you do.”  Cas has put on his parent voice, trying to curb any pushback from Jack.  Of course it doesn’t work.

“What?” Jack seems almost frantic.  “But I _have_ to go tomorrow!  There’s a group of us working on a history project due by fall break, it’s like _half_ my grade.”

“I’m sure your classmates can do the work over here,” Cas sighs, pushing himself to his feet as well.  He hasn’t had to punish Jack much growing up, and he refuses to back down now that he is.

“But we’ve got all our books and everything already set up at Jody’s!  Please Dad, you can ground me on Sunday!”  Cas doesn’t quite know what to make of Jack’s sudden manic devotion to his schoolwork, it just doesn’t sit right in his stomach.

“I have to talk to Jody,” Cas relents.  “No promises until then.”  Jack groans in frustration and storms off to his room, leaving Cas with a headache and a need for a stiff drink.  Grabbing a glass, he fills it with ice before climbing half on the counter to get into the top corner of the cabinet, grabbing his small bottle of vodka.  He doesn’t drink often, his worry that the hospital might call him in keeping him sober, but tonight he just needs the one to calm his nerves.  He pours out a generous amount, putting the bottle away before grabbing the orange juice out of the fridge to mix it with.  It’s a bit more vodka than orange juice and he coughs after the first sip, but he figures he deserves it.  He pulls out his phone and dials Jody’s number, listening to it ring a few times before she answers.

“Hey, Castiel, what can I do for you?” she greets him.

“As if I’m not already in your debt for all the help with Jack over the years, I need another favor.”

“Anything for you, my friend.”  There’s a pause then the sound of Jody yelling from a distance.  “Alex, Claire!!  Phone- knock it off!”  The background noise behind her call goes quiet.  “You sound a little tired,” Jody adds in her normal voice.

“I’ve been exhausted since I started my college nursing program, I can’t imagine that’s going to change for another couple years.”  

“Good point, I guess I should say you sound _more_ exhausted.”  

“That’s why I’m calling.”  Cas takes another long sip of his drink before continuing.  “I don’t know if you noticed, but Jack’s been a little...different lately.”

“I’ve noticed,” Jody’s voice goes serious.  “He’s been hot and cold since the first week of August.  I mean, I deal with trouble kids all the time, never expected to see it from him.”  There’s affection in the way she says ‘trouble’, Cas knows Jody loves all her foster kids and temporary wards like they were her own.

“I actually got an email from his teacher.  First time anything like that has happened, I think.  Apparently this new math teacher and Jack have been at odds all semester.”

“Yeah, Claire was telling me about the new guy.  Apparently he’s a ‘baby faced bro with a superiority complex’, or so she tells it.”  Jody pauses and when she speaks again Cas can hear the cop in it.  “I can’t say I blame him for calling you in for a conference, though.  I mean, I know Jack’s a good kid but he can only push at an authority figure so much before something happens.”

“Funny you should mention that,” Cas chuckles, hardly any humor in it, “I was attempting to ground him, but he said he has school stuff tomorrow?”

“Yeah, I was going to pick him up for you.  If you still need me to?”  Jody seemed to know exactly what was going on, and it just added to Cas’ frustration.

“Yeah, I’ve gotta be at the hospital fairly early.  Just...you’ll make sure he doesn’t goof off, right?  Till I can pick him up?”

“Of course, Cas.  I go into the station at one but Donna’s got the kids.  I’ll make sure she knows.”  There’s a couple beats of silence before Jody speaks again, softer this time.  “I know what you’re doing, Castiel.  You’re trying to figure out where you went wrong as a parent.  Take it from someone who knows- don’t.”  

“I was so young when he was born, Jody,” Cas sighs.  “I was 21, practically just a kid myself, and now I’m 37 and I _still_ know shit about any of this.”

“I ain’t gonna tell you how old I am, but I will tell you that I don’t know everything either,” she laughs.  “You just do the best you can and hope for the best.”   

“Thanks, Jody.”  Cas swirls the liquid in his cup a couple times, trying to take the comfort she was offering him.  “I’ll go let Jack know what’s going on.”

“Okay, talk to you later, Cas.”  Cas hangs up the phone with a weary sigh, finishing off his drink and making his way down to Jack’s room.  

“Jack?”  He hears Jack moving through his room, and the door cracks open slightly, his face expectant when it comes into view.  “Jody will be by to get you tomorrow, and you’ll be staying home on Sunday.  After I talk to your teacher on Monday I’ll decide if anything else is changing.”  Jack just sighs and closes the door, and Cas nearly bangs his head against it.  Would probably do the same amount of good as talking to his son anyway.  With a resigned sigh, Cas made his way to his bedroom, ready to just pass out and get this day over with.

 

“Hey, Sam,” Cas stepped back so the taller man could make his way inside Cas’ apartment early Sunday afternoon.  Meg and Eileen waved in greeting, and Sam’s face lit up when he saw Eileen.  Cas smiles to himself and winks at Eileen from behind Sam.

 _Someone’s happy to see you,_ Cas signs and Eileen grins.

“Hello, Sam,” Eileen said out loud.

 _Hello, how are you?_ Sam manages to sign, and Eileen giggles.

“I’m fine, thank you,” Eileen says, and Sam blushes.

“Wow, flirting much?” Meg says casually, and Sam fidgets awkwardly, which was a feat for a guy so tall.  Eileen glances at Cas who quickly signs what Meg had said, and she giggles as well.

“How’s life been treating you?” Meg asks Sam.

“Well, other than my brother getting on my nerves, it hasn’t been too bad.”

“Your brother just moved in this summer right?” Eileen asks.  Sam nods, obviously pleased she remembers their last conversation

“Yeah, and I mean, we get along for the most part but sometimes he just complains too much.”  Eileen smiles knowingly at Sam, and Cas excuses himself to the kitchen to get lunch ready now that his last guest has arrived.  He turns on the oven to preheat for the frozen pizzas, and when he turns back around he’s surprised that Meg followed him into the kitchen.

“You need something?” Cas wonders.

“So, tell me, why’d you invite Sam over?” Meg asks quietly as Cas pulls the salad mix out of the fridge.

“Because I wanted to be friendly?” Cas starts to dig in a cabinet for a serving bowl.  “I didn’t think I needed an ulterior motive,” he adds.

“Wow...I forgot how simple things can be with you sometimes,” Meg chuckles.

“The hell is that supposed to mean?”

“Oh nothing.”  She winks at him.  Narrowing his eyes, he points at the salad.

“You can at least help if you’re going to bother me.”  She smirks and opens the bag of salad, pouring it into the bowl and getting out Cas’ cutting board.  He pulls the rest of the fresh veggies out for the salad, and he and Meg start to chop them in silence.  Cas’ worry over Jack is continuing to pester him, more than he feels it should, and as he slides the pizza in the oven he can’t keep quiet anymore.  “You know, I was just thinking how much Jack reminds me of Kelly, the way he stubbornly tries to be independant,” Cas points out quietly.  Meg’s knife stills for a moment before she continues to chop the carrots Cas has finished peeling.

“Don’t, Cas.  Don’t go there again.”

“I can’t stop my brain from going there, Meg.  I just-”

“I know me telling you it wasn’t your fault, that there was nothing you could do, isn’t going to help or it would have done so 16 years ago.  But Cas, you did all you _could_ do, and then some.”

“I know,” he sighs, sliding the last carrot over to Meg.  “As my therapist said: ‘depression isn’t logical.’  I hear what you’re saying but it still hurts, even after all this time.”  Meg examines the carrot thoughtfully before she starts to cut into it.

“Whatever is going on with Jack really has you rattled, huh?” she asks, tossing the last of the carrots into the bowl.  

“Something just feels… I know I’m probably just being paranoid, but it feels _wrong._ ”

“It’s a bit of an attitude in a 16 year old,” Meg points out.  “It’s textbook normal.”

“But it’s too sudden, and it’s not like Jack.”  Another pause, neither of them moving.

“It’s not him,” Meg says with certainty.  “It can’t be _him.”_ A chill runs up Cas’ spine, and the oven dings that the pizza is done.

“God, I hope you’re right,” Cas sighs.  He pulls the pizza out and finishes setting up the table, walking back towards the living room to fetch his other houseguests.

“Sometimes it’s the helplessness that’s worse than the guilt,” Sam is saying, and his voice sounds so strained, Cas hangs back for a moment to give him privacy.

“I know that feeling,” Eileen says, “I feel that way a lot, no matter how much progress I make, or how many new technologies make my life easier.”  Cas peeks around the corner to see her reach out and squeeze his hand, and his worry is momentarily forgotten as he smiles at the sight of Sam and Eileen’s budding romance.  

“God, listen to me complaining.  I’m sorry,” Sam says quickly.

“Your worries are valid, Sam,” she says with a smile.  “Besides, I think it’ll be a nice change to have someone to help take care of.”  

“You- you’d like to… I, great!” Sam stumbles over his words, blushing and grinning.  Cas coughs to announce his presence as he steps back into the living room.

“If I’m not interrupting, lunch is ready,” Cas announces.  

“Good, yeah, food.”  Sam jumps to his feet in surprise, and Eileen laughs, getting to her feet as well.

 _Is that what it sounded like?_ Cas signs.  

 _I think it was._ Eileen grins, signing back.   _He’s so adorably awkward, this is going to be fun._

_Never thought of a six foot tall moose man as adorable before._

_Well, maybe you just haven’t found the right six foot tall man,_ she signs with a smirk.  

 _Very funny,_ Cas signs, rolling his eyes, but he knows his blush gives him away.  When Eileen walks out to the kitchen, Cas makes his way down to Jack’s room.  “Lunch is ready,” he calls through the door.

“Not hungry,” Jack calls back.  Cas knows he probably just doesn’t want to eat with the adults, but he needs to at least get some food.  

“Jack, come on,” Cas knocks again.

“Just leave me alone,” Jack grouses, and deja vu freezes Cas’ next knock.

 

_“Just leave me alone!” Kelly shouted through the closed door._

_“Kelly, please, just let me help.”  Cas knocked his head against the door, silently pleading with the woman on the other side.  It took a moment, but she opened the door, her makeup smeared down her face by tears._

_“Cas, I’m...I’m pregnant,” she sobbed.  Cas felt the color leave his cheeks as dread settled like a stone in his gut._

_“Kelly…”  He wrapped her up in his arms as she sobbed till her voice was hoarse, and a cold panic settled into his skin.  “I’m so sorry,” he whispered into her hair, blinking away tears of his own._

_“I can’t- Cas I can’t- what are we going to do?”_

_“I don’t know,” Cas swallowed hard._

 

The raw fear he’d felt at Meg’s suggestion in the kitchen is back, and Cas leans heavily on the wall as it threatens to overcome him.  He hadn’t felt this fear in years, and still it holds power over him like it was just yesterday.  

“What am I going to do?” Cas whispers to himself.

**Notes for the Chapter:**

> Plzzzz leave me some comments, I needs them XD


	3. Chapter 2

**Notes for the Chapter:**

> OKAY FIRST I WANT TO APOLOGIZE FOR TAKING SO LONG!!   
> I had to struggle through some not so fun personal crap, and writing had to take a backseat. :( It's been a rough couple weeks but watching the hits and kudos keep going up on this have kept me motivated to keep trying so thank you so much.
> 
> I've gotten this chapter done and I'm so excited to share it with you!! Fingers crossed the next update won't be so long!

_ Dean _

 

Dean was kinda nervous leading up to the conference Monday afternoon, not that he’d admit it to anyone.  He spent way too much time picking his tie and sweater combination that morning, and had even debated keeping his glasses on and leaving his contacts at home.  Fear of endless teasing from Charlie and Benny stopped that thought quick, but he did pick out his best tie, a silky green one that brought out his eyes, matched with a dark grey sweater and some charcoal slacks, he felt good leaving the house.

Granted, once he got to school he realized he looked like some kid from Harry Potter.  At least it won him some cool points with a handful of his students.  Judging by the subdued way Jack handled himself in class, Dean guesses he was aware of his meeting with his father that afternoon.  It was kinda nice to have an uninterrupted class for once.

When his planning period rolled around, Dean worked on the format of his midterm test he’d be giving on Wednesday as he waited for the time to pass, shuffling the questions into a sufficiently random order and printing out a master copy.  He tucked it safely in his bag, and took a deep breath, watching the minutes tick by as he waited for the last bell to ring.  

What was this Mr. Milton going to be like?  Was he going to be the type of parent to make excuses for their kid?  The type who laughed away this meeting as nothing important?  The type to direct their anger at Dean about their kid being in the situation?

Dean shifts uncomfortably, a bead of sweat dropping from his hairline as he considered the last kind of parent, the one he hoped never walked in that door.  The worst part was it would make sense, he and Jack were fairly similar it really wouldn’t be a surprise if his father turned out to be just like Dean’s.

  
  


 

_ “I don’t care about what he wants,” John’s voice had carried loudly through the house.  Ten year old Dean was huddled at the top of the stairs, and had listened as his father had drunkenly argued with someone on the phone.  “He is my son and he’ll take over this garage like I took it over from my dad.”  Dean hadn’t understood why it was such a big deal when his teacher had asked him about his career day project for class.  He didn’t think it was weird that the other kids had chosen astronauts or doctors, and he’d done his about Winchester Auto and Savage.  Apparently, it was weird enough it made Mr. Singer call his house, and his dad had gotten so angry.  Again. _

_ “Dean?” Sam’s small voice had drifted up from behind him, woken from his sleep by the shouting. _

_ “It’s okay, Sam,” Dean has assured his brother, pushing himself to his feet and turning Sam for his bedroom. _

_ “Who is Dad yelling at?” _

_ “No one, don’t worry about it.”  Dean tucked his brother back into bed, after he walked around at the children’s doctor toys, action figures covered in bandaids.  Sam could become a real doctor someday, and that night ten year old Dean decided he would do anything to make it happen. _

  
  


 

A soft knock startles Dean out of his memory to the point he almost falls out of his chair, and he spins around to face the door to his classroom.  A man is standing there, looking uncomfortably out of place in a well worn button up shirt and beat up old jeans, eyes looking around the room nervously.  He’s got a  _ literal _ mess of dark hair on his head, and just enough stubble on his face to hint at the kind of beard he could grow if he wanted.  Dean belatedly notices the visitor sticker on his shirt and pushes himself to his feet.

“You must be Mr. Milton?” he asks, walking to the door and offering his hand to shake.  The man does, catching Dean’s hand in a firm grip, long nimble fingers closing around his fist.

“Yes, I apologize for arriving early, but I was able to slip away from work sooner than expected.”  Dean steps back, allowing the man to walk past him into the classroom and closing the door behind him.  Dean totally did  _ not  _ check out the guy’s ass, or notice the runner’s thighs attached to it.  Not at all, because he was a  _ professional  _ here to talk about one of his students.  Mr. Milton turns back to face him, eyes looking him over.

Great, now Dean was nervous for a totally different reason.  Dean clears his throat.

“Please, have a seat,” he says, gesturing at the chair in front of his desk.  Mr. Milton sits, body language stiff and anxious, like he’s the one in trouble, not his son.   _ Fuck, did he have to be so goddamn pretty? _

“So Mr. Milton-“

“Cas,” the guy blurts, and Dean blinks at him.  “My name is Castiel, you can call me Cas,” he explains quickly.

“Okay, Cas,” Dean nods.  “As I stated in my email, Jack seems to have formed a certain...antagonistic attitude when it comes to myself.  It’s disturbed class, and quite frankly tried my patience.  This meeting is mostly for me to figure out what’s going on, if it’s something I’m doing or... what.”

“It’s not you,” Cas admits, his shoulders slumping slightly.  “I’m not sure what it is, honestly, but his attitude at home has changed too.”  Jack’s father is young, Dean realizes, not much older than he is, and he can imagine raising a kid so young can’t have been easy.

“Has he mentioned anyone from school specifically?” Dean tries.  “Another kid giving him grief?”

“He hasn’t been telling me much of anything.”  Cas rubs at the back of his neck, and Dean tries not to watch the way his fingers trail down over his collarbone as Cas lowers his hand again.   _ Professional, be a professional. _

“My understanding is Jack’s been at this school the whole time, correct?  No moves or class changes?”

“No, nothing like that.”  Cas pauses to think.  “Nothing has changed for a few years now, honestly.  Same apartment, same neighbors for the most part.”  Dean was stumped, he was  _ sure  _ there had to be some influence on this kid at home, but his gut was telling him this Cas guy was okay, genuinely concerned with what was happening with Jack.

“How is he with friends?”

“He’s got a few close friends he hangs out with,” Cas shrugs.  “I’m sure you probably know a few of them.  They’re not model citizens, but they’re not bad kids, and I’d rather him hang out with them than be somewhere I don’t know where he is.”  Dean was liking this guy more and more, which wasn’t helping with his  _ be a stern teacher  _ approach.  No, he could already feel his teacher persona melting away in front of this dude, which probably explained why he didn’t think too much before asking his next question.

“What about his mother, does she have an idea what might be causing this?” Dean wonders.  Cas’ eyes widen and drop to Dean’s desk and Dean starts to internally freak out.   _ Too personal, abort.   _ “Nevermind, you don’t have to answer that.”

“No it’s fine.  She um, she died when Jack was born,” Cas admits quietly.  Dean’s heart sinks into his stomach at the undisguised pain in Cas’ voice.

“Oh, god I’m so sorry,” Dean blushes, kicking himself for sticking his foot in his metaphorical mouth.  He also realizes it was yet another thing he and Jack had in common, losing their mothers.

“No, don’t be, you had no way of knowing.”  Cas waves the apology away and after a moment sits up straight again, having shaken off the memory.  “I’m afraid I’m at a loss as far as solving this, I welcome any suggestions you might have.”  Dean snaps himself back into teacher mode, subconsciously straightening his tie as he sits up straighter.

‘Well I’ve tried detention,” Dean points out, “that doesn’t seem to be working as a deterrent.”

“Detention?” Cas’ voice snaps, every part of his body going stiff as a board.  He’s  _ furious,  _ Dean realizes.  

“Yeah,” he says slowly, “Jack’s been in Friday detention a few times, as well as Saturday detention this past weekend.  Has he,” Dean pauses, realization dawning on him, “has he not told you?”  

“He has not.”  Cas’ voice is like ice, and is sends a shiver down Dean’s spine.  He’d both hate...and kinda like...being on the receiving end of that.  Dean clears his throat and shakes the inappropriate thought out of his head.   _ Pro-fess-ion-al. _  “What usually happens after detention?” Cas asks.

“In light of you not knowing, I’ll let you talk to him about this before I do anything else,” Dean says quietly, like he’s afraid Cas might lash out.  “And I’ll be sure to personally send you any emails if something in his behavior changes, or if he receives any more detention.”  Cas nods, standing slowly, his eyes not really focused on anything.

“Thank you, Mr. Winchester,” he says, his voice calm when his body language is anything but.  “I will speak with Jack.  I hope he doesn’t continue to cause trouble for you.”  He offers his hand to shake, and Dean takes it, wincing when Cas’ grip is exponentially tighter than the first time.

“Sure.  Email me anytime,” he adds with a smile.  Cas nods curtly, turning on his heel and walking out of the classroom, and Dean feels like most of the oxygen follows him.

That...that was  _ nothing  _ like what Dean was expecting.  Cas initially reminded him of a student more than a parent, with the nerves and the guilt, and he ended the meeting feeling like he was somehow in trouble with Mr. Milton.  Dean distractedly gathers his belongings, locking his classroom and making his way towards the parking lot in a daze.  

“You okay?  You look like you’ve seen a ghost,” Charlie asks, walking up beside him.  

“Yeah, I’m good I...I just finished my conference with Jack Milton’s father.”

“Oh, that bad huh?” she nods in understanding.  “Let me guess he shouted at you all about how it’s your fault that Jack’s been acting up.”

“No, actually.”  

“Oh...well something happened, because you look a hot mess Winchester.”  Dean leans heavily on his car, massaging his forehead.

“I don’t know, the guy was...he was kinda acting guilty at first, then when he found out Jack had been in detention he flipped into this scary, quiet angry vibe and-“  Dean cuts himself off quick but Charlie is smart, even after a few short months she knows him better than he realizes.

“And what, Dean?” she urges, managing to keep her smile in check.  Dean doesn’t want to admit it, but if he doesn’t she’ll just keep hounding him and making this a bigger deal than it is.

“He was...hot.”

“Hot?” Charlie repeats, her eyes popping out of her head.  “Oh  _ do  _ tell.”  

“It’s nothing,” Dean sighs, opening the car door and tossing his bag inside.  

“Is ‘nothing’ code for ‘Dean has a crush on Mr. Milton’?” 

“What? No!” Dean scoffed.  “It’s not a crush, I talked to the guy for 15 minutes.”

“Mmhmm,” Charlie hums knowingly, and Dean rolls his eyes, dropping into the driver’s seat of the Impala.  “I want to be your best woman at the wedding!”  Charlie called as he started the engine, and he flipped her off out the window as he pulled away.

The problem was, thoughts of Castiel Milton didn’t go away.  They plagued Dean all through his drive home, the way his heart had reached for Cas when he was talking about Jack’s mom, the way he wanted to set his nerves at ease.  The curve of his ass in those old ratty jeans… Dean hadn’t dated anyone in a  _ long  _ time, as his brother frequently pointed out one night stands with no intention of seeing them again didn’t count as dates.  If it had just been Cas’ looks that had distracted him, it would have been easy for Dean to just ignore him, but something about Cas… 

_ Fuck my life.   _ Dean ran his hands through his hair, unwilling to believe he was falling into the trap of this romantic bullshit.  He’d barely spoken to the guy, he didn’t  _ really  _ know anything about him, this was nothing but a lonely Dean seeing a hot guy and wanting to get his dick wet… right?  Not to mention he needed to avoid falling into this rabbit hole at all with Cas because the dude was the  _ father  _ of one of his students.  That was a bad idea in all sorts of ways, he was sure of it.

Dean groans in frustration, knocking his head against the steering wheel when he stops at a red light.  Go figure the first person he’s even remotely been interested in is someone he can’t even go after.  A honk from the person behind him startles Dean and he continues driving home, lost in the memory of strong warm fingers wrapped around his own.

 

*****

_ Cas _

 

Cas walks through the hallway of the high school in stunned silence.  He’s angry with Jack, yes, but he’s also angry with himself for not seeing this was happening in the first place.  It’s his son for crying out loud, he  _ knows  _ him, so why was he completely blindsided?  Cas heads for the visitor parking, where Jack is leaning on the passenger door of his car, guilt written in the slump of his shoulders.  When Cas walks up, he looks up and opens his mouth to talk, but Cas cuts him off with a glare, unlocking the doors with the key fob.  Jack keeps his silence, climbing inside the car and buckling into his seat, leaning his head on the window as Cas pulls away from the school.  

Cas focuses on the road, on the cars around them, the kids walking home, and uses it as an excuse to push aside the conversation he needs to have with Jack.  He just wants a moment to think this through, because the last thing he wants is to unwillingly make this whole attitude thing worse.  His relationship with Jack lately has been on rocky footing at best, he doesn’t want him to completely shut down.

They’ve made it home without saying a word, but as soon as the door closes behind them, it’s like a damn breaks, and Cas can no longer avoid this conversation.

“Were you going to tell me about the detentions?” Cas asks, and Jack sighs heavily, tilting his head to look at the ceiling before facing his father.

“Probably not?”  He glares at Cas from underneath the lock of hair that keeps falling over his eyes.  Cas has been meaning to get them both a haircut for some time now, but he just hasn’t had the time.

“Jack, this is serious.  Discipline goes on your record, and colleges will see those sorts of things.”  Cas takes a deep breath to keep his voice even.  “I know it doesn’t seem important now, but getting into a good school can make a huge difference in your future.”

“My future?”  Jack scoffs, crossing his arms as he frowns at Cas.  “So that’s really all you’re angry about?  Just that I might be ruining the perfect future you’ve come up with in your head for me.”

“Is it so hard to believe that I want good things for you?”  Cas‘ voice isn’t raised, though there’s no less anger in it.  “Do you really want all the hard work you’ve put in up till now to just be flushed down the drain?”

“Why does it even matter to you?!” Jack shouts.  “It’s my life, what if this is what I want to do with it?!” 

“Because I’m your father!”  Cas shouts back.  Jack’s eyes go wide and Cas takes a calming breath while he counts to ten.  He’s hardly ever  _ shouted  _ at Jack before, mostly because he’s had no reason to.  “I just don’t understand why you kept this from me,” Cas continues in a calmer voice.  “We’ve always told each other everything, Jack, haven’t we?  I promised you when you were little I will always answer every question you have, about everything, and I meant it.”

“Even Mom?”  Jack’s voice is accusational, and the cold trickle of dread Cas had felt a few weeks ago shows back up at the base of his spine.

“Yes, Jack.”  Jack turns away and paces a few steps, and Cas waits cautiously.

“Did you love her?”  Cas almost doesn’t hear Jack ask, and he immediately wants to reach out and hold him tight, to protect him like he did when he was a little boy.

 

 

_ “Why did mommy leave?”  The question was innocent, but Cas had stared down at his five year old son in sudden terror.  He knew the questions would come but he hadn’t exactly prepared for them that early. _

_ “Why are you asking that?” Cas wondered, as he watched Jack scribble in a coloring book. _

_ “My friend Ryan said his daddy was leaving, and that my mommy must have left too.”  Jack’s big eyes had looked up at him in curiosity. _

_ “Your mommy got sick,” Cas explained carefully.  “She loved you very much and didn’t want to leave you, but she had no choice.” _

_ “Is she gonna come back when she gets better?” Jack had asked.   _

_ “No, buddy.”  Cas’ eyes had clouded with tears, and he’d blinked furiously to keep Jack from seeing.  “No, she won’t be back.” _

  
  


 

“I did love her,” Cas admits.  “And I still miss her.”  He watches as Jack’s shoulders sag slightly, and when he turns around he looks more like himself than he has in weeks.

“I’m sorry about the detention,” he relents, “but I stand by the fact that this new teacher is picking on me.”

“I’ll keep that in mind.”  Cas crosses his arms, looking pointedly at Jack.  “No visiting your friends outside of school until the month is over.”

“Two whole weeks?!” Jack complains.

“Yes, bare minimum.  And if I email your teacher and ask about detention I better not find out you’ve been given any more for the rest of the semester, or we’ll start talking cell phone privileges, too.”  Jack scowls as he stomps off to his room, but he doesn’t slam the door, which Cas will take as a sign he knows he’s getting off light.  Scrubbing a hand over his face, Cas tiredly heads for his own room, dropping face first into his pillows with a groan.

His phone rings, vibrating in his pocket, but he ignores it, not moving except to turn his head to the side so he could breathe.  It rings again, and with a groan he pulls it out and checks the caller ID.  

“What?” he answers with a groan.

“Wow.  Here I am calling to check in with my friend and that’s the kind of reaction I get?”

“Meg, I’m not exactly in a good mood,” he grumbles, rolling over onto his back to make talking easier.

“That’s what I was calling about,” she chuckles.  “I take it the meeting with the teacher went as well as expected?”

“Jack’s been in detention, and he didn’t tell me.”

“That makes me proud of the kid,” Meg hums.  “He  _ does  _ know how to get in trouble!”

“Meg-”

“I’m just saying, I thought I’d never rub off on him.”  Cas wants to stay angry, but Meg’s banter helps him relax. 

“At least tell me you didn’t know about it?”

“I didn't,” she assures him.  “So, the teacher himself?  What was he like?”

“He was…”  Cas pauses.  He hadn’t actually thought about it, he was so distracted by what was going on with Jack.  He remembers being struck by the guy’s age, older than he’d expected for a first time teacher.  There was a confidence, almost a swagger in the way he carried himself, something Cas has desperately wished he could develop.

“Earth to Cas?  Where’d you go, Jupiter?” Meg interrupts.

“Sorry, I just...I was trying to find a way to describe him.”

“Well, start with the basics.  Short, tall, fat, skinny?”

“Tall, taller than me by a couple inches.  In shape, though he was wearing a sweater.  Green eyes, like, really green.  Calloused hands, laugh lines around his eyes.  His jawline reminds me of Sam…”  Cas takes all of three seconds to put the name of Jack’s teacher together with the name of one of his close friends.

“Sounds absolutely dreamy,” Meg continues, oblivious to Cas’ epiphany.

“Fuck me,” he groans.

“Been there, done that.”  Meg snorts a laugh.  “Dude, where the hell did that come from?”

“The- he’s- I… Meg I think he’s Sam’s brother.”

“You think, Sherlock?”  She’s laughing now, and Cas flushes in embarrassment.

“You knew since you saw his name on the email, didn’t you?”  Cas

“I did, because unlike you I didn’t go into a panic and had the presence of mind to talk to Sam about it.”

“Damn it, now every time I see Sam I’m gonna think about his-”  Cas cuts himself off but it’s too late.

“So I wasn’t far off with the dreamy comment,” Meg giggles in delight.  Cas wants to deny it, but she’s right.  Sam’s brother was, quite honestly, gorgeous.

“Well, shit,” Cas sighs.

“What?”

“I don’t even know his name.”  Meg’s laugh rings out loud and long, and Cas can’t help but smile.

 

**Notes for the Chapter:**

> THEYVE MET WHOOO HOOOO
> 
> What happens now?!? GUESS YOU'LL HAVE TO KEEP AN EYE ON THIS TO FIND OUT ;)
> 
> Thank you so much for reading and commenting I appreciate it so much <3


	4. Chapter 3

**Notes for the Chapter:**

> NO THIS IS NOT AN APRIL FOOLS JOKE THIS IS A REAL UPDATE!!
> 
> I apologize profusely for taking so long but here it is at LAST!! The next update shouldn't be quite so delayed *nervous laugh*

_Dean_

 

Dean didn’t know who was more excited for the short fall break coming up, him or his kids.  Deciding not to make his students hate him, Dean had given his large quarter-year test the day before, putting on a movie and allowing the kids to goof off on their last day of classes.  Most of them seemed to know how much of a gift he was giving them and kept fairly well behaved, all things considered, and Dean was able to catch up on his email and some paperwork for the school.

Just before his sixth period class ended, he noticed Jack and Claire huddled together talking about something.  She seemed agitated, like she was trying to convince Jack to do something, and Jack wasn’t having any of it. Dean wanted to intervene, but given their history, he was sure Jack wouldn’t react well, so he let it be.  Eventually Claire angrily moved to another desk, and Jack put his head down on his, and Dean couldn’t help it, his heart went out to the kid. Since the conference with Cast- _Mr. Milton,_ Jack’s behavior has become tolerable, and Dean is relieved he hasn’t had to email Jack’s father again.  Totally, 100% relieved that he doesn’t have a single excuse to communicate with him in any way.

Dean nearly knocks his head against his own desk.

When the bell rang, Dean called Jack over, Claire hesitating in the doorway until Jack waved her away.

“What can I do for you, Mr. Winchester?”  Dean ignore the attitude in Jack’s voice.

“I just wanted to take a moment and thank you for improving your behavior these last couple weeks.”  Dean smiles when Jack’s scowl is replaced with surprise.

“Uh, thanks, I guess,” Jack shrugs, his hand fiddling with his bag strap.

“I know we started off on the wrong foot,” Dean goes on, “but I want you to know I don’t hate you, contrary to what you might think.  It might surprise you to know I was almost exactly like you in high school.”

“So, what, we’re supposed to bond over how crappy a student you were, too?”  Jack’s scowl is back, the moment of vulnerability lost. “If you’re going to feed me some stupid crap about how you ‘turned out okay’, I’ll pass.”  Jack turned for the door.

“I lost my mother, too” Dean blurts, and it makes Jack pause.  “Raised by a single father who thought he knew what was best for his kids.”  Jack doesn’t turn around. “Listen, Jack, I’m not trying to be your best friend, but if you need anything…”

“Yeah, I get it.  Thanks, but no thanks for this little bonding moment.”  Jack quickly leaves the classroom, and Dean sighs heavily as the door closes behind him.  Well, at least he tried.

Gathering up all the tests and everything he’ll need for the weekend, Dean decided to call it a day, stopping by the main office to check out and walking to his car to head home.  

Sam’s on a night rotation for the weekend, so he’s already gone to work by the time Dean gets home from school.  Taking advantage of the empty apartment, Dean changes into sweatpants and a ratty old tshirt, ordering a pizza for dinner since Sam won’t be around to judge him.  He grabs a beer and has just popped it open when his phone rings. The ringtone (the Eleventh Doctor’s theme) tells him who it is without him even looking.

“Hey, Charlie, what’s up?”

“Hey, I noticed Jack seemed a little distracted in my class today, and I think my class is the only one that he actually enjoys.  Has something else happened?”

“He was arguing with the Novak girl, Claire, during my class period but nothing disruptive.”  Dean sips at his beer. “Why are you calling _me_ about this anyway?”

“Well, I know you’ve kinda taken a shine to the kid-”

“A shine?  Charlie he hates me.”

“Don’t argue with me, Winchester, you know you care about him.”  Dean scowls but he has to admit she has a point. “And anyway, if there had been another problem I was going to give you some pointers on contacting Alex’s dad.  You know, the one you haven’t been able to stop talking about?”

“That’s- I’m not-” Dean’s voice cracks and he clears his throat, bringing his voice back to it’s normal pitch.  “I have no idea what you’re talking about.”

“Mmhmm.  You know… you could just call him.”

“Yeah, okay,” Dean snorts, “because that’s not unethical, or awkward, or anything.”

“It’s not _unethical_ ,” Charlie scoffs, and Dean can feel her eye roll through the phone.

“I’m his kid’s teacher, Charlie, aren’t there rules and shit like that?”  There’s a long enough pause that Dean checks his phone to make sure the call hadn’t dropped.  “Charlie?”

“Okay, so don’t get mad at me or anything but after our last conversation where you ‘totally didn’t’ talk about Jack’s dad I...did some digging.”

“You what?”

“Well, you were all twitterpated, and I know you weren’t going to do anything about it, so I just thought I’d check the rules for you.”  She sounds almost crestfallen, and Dean takes a deep breath, knowing her heart was in the right place anyway.

“Well you gonna leave me hanging here?!”  He isn’t even embarrassed by how desperate he sounds at this point.

“Oh!  Right, yeah, I, uh, combed through the County teacher’s handbook backwards and forwards, along with the teachers union contract...oh!  And checked for any previous civil suits filed in the county. Basically, there’s nothing there. You can totally go hunt down that DILF Mr. Milton!”  Dean’s insides are doing something weird, a mix of excitement and anxiety giving him a stomach ache.

“That’s great and all but, Charlie...I don’t even know the guy.”

“But you _want_ to, don’t you?”  Dean opens his mouth to object, but…

“Damn it.”  He slumps in defeat, because hell yes he wants to get to know this guy, more than the fact that he has the perfect ass.

“That’s what I thought.”  Charlie is gleeful in her victory, and Dean can picture her shit eating grin.  “So, you technically have the guy’s number…”

“No, what?!  I’m not cold calling the guy using the school’s information, that’s just creepy.”

“Wow, you are such a baby.”

“Shut up, this is all your fault anyway.”

“And one day you’ll thank me for it.”  She sighs heavily. “I know we haven’t known each other that long, but I think getting yourself out there would do you some good.”  Dean’s indignation softens with her genuine concern, and he rubs his fingers tiredly along his forehead.

“I don’t know, Charlie, he’s Jack’s Dad.  Don’t you think that’ll make things more awkward between us?”  There’s a knock on the door and Dean retrieves his pizza from the delivery kid.

“Maybe Jack seeing you outside of a teacher roll will help him get to know you, make him see he doesn’t have to mouth off just to prove himself to you,” Charlie’s voice is reasonable and it makes Dean want to believe it.

“And you’re totally sure there’s no rule I’d be breaking?”

“None, you worry wart.”  Dean hears an electronic beeping in the background of the call.  “Crap! Okay, I gotta go, my guild is asking me to help them clear this dungeon.”

“Nerd,” Dean chuckles.

“Whatever.  Just let me know when you set up your first date!”  She hangs up before Dean can say anything else, and Dean groans, grabbing his beer and downing half of it in one go.

  


Dean wakes up suddenly, disoriented to the point he almost falls out of bed.  He’d been dreaming about a bar, and about teaching Castiel how to play pool. It was a nice dream, and yeah, maybe it was a _nice_ dream, too, but whatever, Dean couldn’t control his subconscious.  The harsh ring of his phone pierces his eardrum, and he grabs for it, jabbing at it with his thumb till he answers the call.

“The hell do you want, it’s 3:30 in the morning,” he grouses.

“Sorry to disturb your beauty sleep,” Sam scoffs, “but I need you to come pick me up from work in an hour.”

“Wait, what?” Dean tries to shake the sleep out of his head.

“My car won’t start, and yes, before you ask, we tried jumping it, I checked the spark plug, and the battery is relatively new.”  Dean turns on his bedside light to try and keep himself from falling back to sleep.

“So you buying that crappy Honda whatever, which I told you not to buy in the first place, is suddenly _my_ problem?”

“Look, I’ve already called AAA, the tow truck is on it’s way to take it to the nearest garage, but no one will be able to look at it till Monday.”  A memory surfaces at Sam’s words.

  


_He was elbows deep in an old Dodge, and he was half tempted to climb the whole way in if it meant he’d avoid that conversation._

_“I asked you a question,” John snapped, and he drew himself up to his full height, the letter nearly crushed in his fist._

_“It’s an acceptance letter.  I’m going back to school.”_

_“The hell for?”_

_“Dad, I can be more than this,” Dean had said.  “I can do more with my life, like Sam.”_

_“And what about me, huh?”_

_“You’ve got Garth, Ash, Roy, and Walt, it’s not like you really need me.”_

_“Your brother put these ideas in your head,” John had seethed, “and now you’re abandoning your family for this bullshit.”_

_“Sammy is family!” Dean shouted as he climbed out of the car and tugged his work overalls off.  “Too bad you forgot that when he refused to listen to you.” Dean turned and walked towards the exit._

_“You walk out that door I best not see you walk back through it again!”  John’s shout rang loud in Dean’s ears, but he walked out just the same._

  


“Fuck the garage,” Dean grunts, pushing himself to his feet and out of his memory.  “Have them bring it here, I’ll fix the damn car, and you can pay _me_ the money you would have paid those garage assclowns.”

“Assclowns?”

“Shut up, Sam.”

“Dean, I gotta get back to work, are you coming to get me or not?”

“Yes, I’ll come rescue you,” Dean scoffs.

“Okay, my shift is scheduled to end at 4:30 but if something comes up I might have to stay on a bit longer.  See you in a bit!” Sam is already talking to someone else as he hangs up the phone, and Dean digs his knuckles into his eyes.  

It’s Sunday, the last day of his short break, and he was supposed to be sleeping late and doing absolutely nothing, having finished grading the last of the tests last night.  Nope, apparently he has to get out of bed before the sun and go fetch his moose of a brother because he decided to buy some cheap, crappy import instead of a decent car.

He pulls on his jeans from the day before, grabbing a clean t-shirt and tugging a blue plaid flannel on over top, not even bothering to try and fix his sleep mussed hair before making his way out to the kitchen.  The coffee can isn’t on the counter, so Dean goes into the pantry.

It isn’t there either.

“Fuck me,” he groans.  They’re out of coffee. Sam wakes him up at three fucking thirty and he had used the last of their coffee.  Grabbing his messenger bag so he can pretend to at least be productive, he tugs on his shoes and leaves for the hospital early, figuring he can grab some coffee and breakfast when he gets there.  The only saving grace is that at least there’s no traffic on the road, and he makes it to the hospital in decent time, parking and making his way inside. He stops by reception to have them page Sam and let him know Dean was there, and walked to the little cafe.

After two cups of coffee and two donuts, Dean has effectively claimed one of the tables as his own, still fairy close to the coffee pot incase he needs a third cup.  It’s an hour past when Sam’s shift was supposed to end and Dean’s grateful he had the presence of mind to grab his bag when he left the house half conscious. He’s going over his upcoming lesson plans and trying to figure out what’s going to be on his midterm when he senses a presence walking up to his table.

“About damn time,” Dean huffs, “we should get something to eat before we head home.”  Dean finishes a note in his planner before glaring up at-

Oh, that wasn’t Sam.

“Sadly, I have to get home, otherwise I’d take you up on that offer.”  The man raises an eyebrow at Dean over his fresh cup of coffee. He was wearing scrubs and an ID badge and Dean’s brain starts to stumble over itself when he recognizes the tufts of dark hair and the blue eyes.

“Mr. Milton?!” he blurts.

“I told you, call me Cas,” he says, setting his overstuffed messenger bag down and pouring himself a cup of coffee.  

“I, uh, I just...you’re a nurse.”  Dean can feel his ears turn red as he forgets how to English, but Castiel- Cas- simply smiles.

“I am a nurse, yes.”  Castiel sips at his coffee and sighs.  “I take it I’m not the one you were expecting.”  He looks over at Dean, cradling his cup in both hands.

“No, I, uh, I’m waiting on my brother, he’s running a bit late,” Dean explains.  

“Is your brother Sam?” Cas asks.

“Um, yeah, you know him?”

“It’s a big hospital, but not that big,” Cas shrugs.  “Besides, not many people with the last name Winchester either.”

“Ah, makes sense.”  Cas stands there stiffly as Dean scrambles for something else to say, and when no words seem to come to him Cas fidgets slightly before picking up his bag.

“So this is...weird.  I’m just gonna, I’m gonna go-“  Dean could kick himself because Cas was _right there_ and he was about to let him walk away.

“No, wait!” Dean blurts, pushing himself to his feet suddenly.  Cas turns back to face him with a bemused look. He has a dusting of stubble over his cheeks and shadows under his eyes, and he just looks _tired_.  Dean’s next sentence comes easy.  “I just, you should sit for a bit.  Being on your feet all day you’re probably exhausted.”  He gestures back at the table lamely, hoping against hope he wasn’t being too creepy or awkward.

“You sure?” Cas asks.  “I won’t be a bother?”

“No, of course not,” Dean assures him.  “I’m just going over some lesson plans.”  Cas still seems hesitant, so Dean tries his best disarming smile.  “Take a load off, Cas.” Cas hesitates for a moment more before setting his bag down next to Dean’s table, dropping into one of the empty chairs.  Dean sits back down, pulling his planner closer to him so Cas has room to set his coffee down.

“Thanks,” Cas says, and Dean doesn’t miss the small sigh of relief when he relaxes into the chair.  “How was your break?” It takes Dean a moment before he remembers Cas would know about their school break because of Jack.

“Nice and boring, just grading tests mostly.”

“Boring is a good thing?”

“Yeah,” Dean smiles.  “When school is going on I don’t get a lot of time to myself.”

“I know the feeling,” Cas says almost to himself.  He looks up at Dean, and Dean can’t help but feel he’s getting the same once over he gave Cas.  He shifts in his chair, but doesn’t look away when Cas meets his eyes. “With no less awkward way to ask this, I’m afraid I don’t know your name?”  

“Wow, sorry Cas,” Dean laughs and Cas smiles too.  “My name is Dean.”

“Dean,” Cas repeats.  “A lot easier to swallow than Castiel.”

“I like your name,” Dean blurts.  “It’s...different.”

“Different?” Cas hums.

“Not _bad_ different,” Dean clarifies quickly.  “Just, you know, something that stands out, something memorable.”  Cas hums at that, fingers idly turning his coffee cup.

“Sometimes a face is so memorable I don’t need a name,” Cas shrugs with a small smile, and before Dean can figure out if that was about _him_ Sam finally shows up.

“Hey, Cas!  I see you met my brother, Dean!”  Sam claps Dean on the shoulder and Dean brushes his hand off, for some reason embarrassed by it.

“Yes, he’s been decent company.”  Cas is looking up at Sam, thankfully, so he doesn’t see Dean blush.

“Alright, Sammy let’s hit the road,” Dean huffs, scrambling to get his stuff gathered.  In his hurry, his messenger bag flips, and a good number of his graded tests slide out across the table.  Cursing and flushing crimson, Dean scrambles to gather them up as Sam laughs. Cas starts to help gather them up, but he pauses after a moment.

Dean looks over and sees Jack’s test poking out of the top of the stack, the letter _D_ in bright red ink clearly visible.

Dean’s stomach drops into his feet as Cas slowly hands him the papers, an unreadable expression on his face.  The fact that he was Jack’s teacher surged to the forefront of his mind, and he feels utterly stupid for even thinking Cas would see him as anything _but_.  He was a father, and that was going to come before anything he would be to Dean.

“Oh, shit.  Cas, I totally forgot I was supposed to take you home before my car crapped out on me.”  Sam turns to Dean, puppy eyes already activated. _Oh shit_ , he wants Dean to give Cas a ride _home._

“It’s fine, Sam,” Cas says quickly.  “The bus runs in about an hour, it’s not like it’ll be the first time I’ve taken it.”

“An hour?!  Dude that sucks.”  Sam glances at Dean with a look that says he knows he’s about to get in trouble.  “I’m sure Dean can drop you by your apartment real quick, it’s no problem.”

“No, I don’t want to be a bother,” Cas insists.  Sam isn’t going to let this go, so Dean figures he might as well step in.

“It’s fine,” he says, trying to make sure he doesn’t sound like he’s freaking out.  “Not a problem.”

“You sure?” Cas is looking at him again, his face unreadable. “I mean, I don’t mind waiting.”

“Course I’m sure, taking the bus is lame.”  Dean waves away his objection, even if on the inside he’d like nothing more than to leave both Cas _and_ Sam behind.

“Okay, great!”  Sam claps his hands together smiling at them both.  Dean nearly slaps the smile off his face. As if things weren’t awkward enough with his failed attempt at making conversation with Cas, now he was going to be stuck in a car with him for the foreseeable future.

Fan-fucking-tastic.

 

*****

_Cas_

 

Cas chats with Sam about his day quietly as they walk through the parking lot behind Dean.  

_Dean._

Cas had been wondering about his name for weeks, and Dean wasn’t exactly what he was expecting, but it fit.  Simple, straightforward, yet it sat pleasantly on his lips, easy to say… Cas wants to smack himself for the direction his brain keeps turning.  He’d made an utter fool of himself, almost _flirting_ with Dean over a cup of coffee like in those trashy stories Meg reads, and his brain just won’t stop.  Naturally, Jack’s test had popped up and now things were nice and awkward, there was no way Dean would consider even going on a single date with him.  Not only was Dean way out of Cas’ league, he was the father of one of Dean’s students.

Doesn’t stop his mind from continuing to wander as they walk, thinking about the dusting of freckles, the too plush lips, those green eyes, and the cute way his blushes start from Dean’s ears then work their way to the rest of his face.

God, what was _wrong_ with him?  Jack's poor grade had hardly even registered, his mind too distracted by the man in front of him.  Even now he’s struggling to focus on Sam’s voice, because apparently he has a thing for bow legs… well, at least this set of them, anyway.  It was too bad Dean didn’t have much of an ass to speak of…

“Do you want the front or the back?” Sam is asking, and Cas finally snaps out of it, finding himself standing next to a sleek black muscle car, obviously a few decades old.

“Um, backseat is fine,” he says, and Sam moves to the front passenger seat, leaning in to unlock the back door for him.  Dean’s already in the driver’s seat so Cas quickly climbs inside, his senses immediately bombarded with the smell of leather and the musky scent of _man._  

“So where to?” Dean asks, starting the car.  The engine roars to life and it startles Cas slightly, vibrating up through his feet and into his bones.  “Cas?” He looks up to give directions he can see Dean’s smirk.

“We live down Kirkman Road,” he explains, and Dean nods, pulling them out of the parking lot and turning south.  

“The tow truck will drop my car off in a few hours,” Sam says to Dean.  Cas is only half listening, watching the city go by as they drive down the almost empty streets.  

“I can’t promise I’ll get it fixed quick, with school back in session,” Dean answers Sam.

“I get that,” Sam sighs tiredly, like he’s had this lecture a hundred times before.  

“Wait, you fix cars?” Cas blurts.

“Been doing it my whole life,” Dean nods, glancing at him in the mirror.  “You seem surprised.”

“Sorry, I just...I didn’t really picture you doing that.”  Cas shrugs, and Dean smirks.

“Didn’t really picture you being a nurse,” Dean shoots back.  Sam’s gaze bounces between them, obviously confused, and Cas turns away to hide his embarrassment.  

“Did you...have you guys met before?” Sam wonders.  Cas fidgets with the strap of his bag.

“He’s my son’s math teacher,” Cas admits.

“Yeah, I uh...that conference I mentioned to you…”  Dean seems embarrassed, though Cas isn’t sure why.

“That’s awesome!  And kinda hilarious,” Sam laughs, and Cas stares at him incredulously.  “I mean it!” Sam turns to his brother. “Dean, Cas is my best friend, I’ve been meaning to introduce you for a while, but the timing of our shifts is always off.”  Dean looks back and Cas manages a weak smile.

“It’s a pleasure to meet you, Dean,” he says, and Dean laughs.

“Back at you.”  Dean turns back to Sam.  “So about my fee for fixing your car…”  The brothers start to bicker about Sam’s car, and Cas loses track of the conversation, trying to tell himself he’s just _tired_ , and that’s the only reason he’s having trouble focusing.  It’s not that he’s picturing Dean in greasy jeans and a dirty t-shirt, bent over the hood of this particular car, sweaty and determined as his muscles bunch and-

 _He’s my son’s math teacher._  His own words echo back through his brain and he slumps back against the seat in defeat, his ill time fantasy quelled by the common sense of reality.  Taking a few deep breaths, he forces his brain back into being responsible, and Jack’s test score comes to mind. He thought Jack’s problem had started to fix itself, after all he’d been a little more his usual self at home lately, but apparently instead of acting out he’s now simply neglecting his coursework.  Cas makes a mental note to ask him about it when he’s had a chance to get some sleep.

“Cas?”  He blinks and looks up at Sam.  “Hey, man, you okay?” They’re at his apartment complex already, and he feels embarrassed that Sam had to tell Dean how to get there.

“Yeah,” Cas says quickly, climbing out of the car and heading for the stairs.  He pauses, turning back to look at Dean through the car window. “Thank you, for this.”  Dean smiles, and it should _not_ make Cas’ insides do a weird dance.

“Sure thing, Cas.”  The brothers wave and pull away, and Cas tiredly stumbles up the stairs and into his apartment.  Jack is passed out on the couch, a game controller resting precariously on his chest as it moves in slumber, and Cas smiles fondly, a memory creeping up on him.

  


_“Okay, okay, he’s asleep,” Cas hissed as he shooed Meg out of the room, the baby monitor in his hand._

_“What are you going to do when I eventually move out?” Meg chuckled._

_“Don’t remind me.”  Cas has walked to the couch and collapsed, sure he was about to pass out.  He had barely managed to lift his arm, the baby monitor settled next to his ear and Cas sighed._

_“You are well and truly wrapped around that little cherub’s finger,” Meg had shaken her head in amazement, but Cas remembered feeling nothing but pride._

_“He’s my son,” he said assuredly._

_“What happened to living free, backpacking around the country...you know that thing you’ve been planning on doing since forever?”  Her voice had bordered on accusatory, but Cas had known there was no real venom to it._

_“That all changed when Kelly got pregnant,” he pointed out, and Meg had shut up after that.  They sat in silence, Cas had listened to Jack breathe, and in that moment he’d felt the world around him change._

  


Cas sets the controller on the coffee table before heading to his room, setting his bag next to his laundry hamper and shucking his clothes, pulling on a pair of sweatpants and falling into bed.  As weird as his day had been, Cas was feeling torn between the kid in the living room and the man with the green eyes. Being Jack’s father would always come first, there was no doubt in his mind about that, but Jack was getting older, and in a couple years he’d be off to college.  Cas hadn’t wanted anything for himself since Jack had come into his life, but then he’d met Dean and suddenly he found himself _wanting_ , on a few different levels.  

Wondering how weird it would be to reply to Dean’s email asking for his phone number, Cas opens his gmail account.  He deletes the usual spam as he tries to work up his courage, but then something in his inbox catches his eye. The email address itself is odd _,_ the username was the word _anonymously_ but it was a gmail account _._ Knowing it’s probably just another one of those annoying porn spams, something makes Cas open the email anyway.

 

_You really thought you could hide from me forever?_

 

One sentence, and his blood runs completely cold, a terrifying panic gripping him.  He drops his phone, scooting away from it and falling out of bed, continuing to scoot till he’s backed into the corner of his room.  He hugs his knees, shutting his eyes and trying to breathe.

Meg.  He has to tell Meg.

Eventually his body relaxes enough to allow him to move forward.  He doesn’t even want to _touch_ his phone but he shakily crawls back over to it, quickly deleting and blocking the email before he pulls up messenger.  With trembling hands, he pulls up Meg’s conversation and types.

 

_You: He found us._

 

Three terrifying words he hoped he’d never even have to consider, were now a reality.  He waits, watching the screen as it comes up delivered, then read, then watches the three grey dots.

 

_Meg: Oh god._

_Meg: What are we going to do?_

 

Cas takes a deep breath and tries to think, his brain focusing on the sleeping baby in his memory and the sleeping teen in his living room.

 

_You: Protect him.  Whatever it takes._

**Notes for the Chapter:**

> Sorry about the cliff hanger ha ha ....

**Author's Note:**

> Okay fam, remember comments are my drug, they motivate me, bribe me, and push me to deliver for you all!
> 
> So...leave me some? Kthxbai! <3


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